Canadians Milos Raonic and Denis Shapovalov are off to the third round in Melbourne as Raonic will take on Frenchman Pierre-Hugues Herbert, while Shapovalov faces world No. 1 Novak Djokovic for the first time. 

Naomi Osaka vs Su-Wei Hsieh – LIVE ON TSN3 at (approx.) 7 p.m. ET/4 p.m. PT

The No. 4 ranked Osaka and No. 28 ranked Hsieh are both coming off straight sets wins in the second round. Osaka and Hsieh have faced each other once before, in 2015, when Osaka won in straight sets. Osaka has won six of her last eight matches on hard court. 

Kei Nishikori vs. Joao Sousa – LIVE ON TSN3 at (approx.) 8:30 p.m. ET/5:30 p.m. PT

Nishikori, the world No. 8, and Sousa have both played two five-set matches already in the tournament. Nishikori recently won the ATP Brisbane International. They have played each other twice before, with both winning one match each.

Dayana Yastremska vs. Serena Williams – LIVE ON TSN3 at (approx.) 9 p.m. ET/6 p.m. PT

Williams, who is currently ranked No. 16 in the world, won her second-round match over Canadian Eugenie Bouchard in straight sets. Yastremska won her previous match in three sets. Williams has won the Australian Open seven times in her career, with the most recent win coming in 2017. This will be the first time that Williams and Yastremska will face each other in their careers.

Novak Djokovic vs. Denis Shapovalov – LIVE ON TSN2/3 at (approx.) 10:30 p.m. ET/7:30 p.m. PT

The No.1 ranked Djokovic takes on the Canadian Shapovalov in the third round of the Aussie Open. Both are coming off straight-set wins in the second round. Shapovalov has never faced Djokovic, a six-time Australian Open winner, before in his career.

Milos Raonic vs. Pierre-Hugues Herbert – LIVE ON TSN5 at (approx.) 11 p.m. ET/8 p.m. PT

Raonic is coming off a big win against Stan Wawrinka in the second round as he eliminated the 2014 Australian Open winner in four sets. Herbert beat the No. 24 seed Hyeon Chung in the second round. This will be the first time that Raonic and Herbert will face each other in their careers.

Alexander Zverev vs. Alex Bolt – LIVE ON TSN.ca & TSN App at (approx.) 3 a.m. ET/Midnight PT

Zverev, the No. 4 ranked player in the world, and Bolt are coming off five-set second-round wins. Bolt is looking to make it to the fourth round of a Grand Slam for the first time in his career, while Zverev is looking to do it for the third time. Zverev has won five of his last six matches on hard court. This will be the first time Zverev and Bolt face each other.

Simona Halep vs. Venus Williams – LIVE ON TSN.ca & TSN App at (approx.) 3 a.m. ET/ Midnight PT

World No. 1 ranked Halep takes on Williams, who is unseeded at a major since the 2014 Australian Open. Both players needed three sets to win their second round matches. Williams holds a 3-2 lead over Halep in their matches, but Halep has won their last two meetings.

Karolina Pliskova vs. Camila Giorgi – LIVE ON TSN.ca & TSN App at (approx.) 5 a.m. ET/2 a.m. PT

Pliskova a former No. 1 currently ranked No. 7 won her previous in three sets while the No. 27 Giorgi won in straight sets in the second round. Giorgi has never made it past the third round of the Australian Open. The two have faced each other five times in their careers, with Plikova winning four times.